Methanol → HCID 58503866, Verbindung

HRID 623810

Reaktionsgleichung

Reaktionsgleichung von HRID 623810
[H-].[Na+].CO.[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12](Cl)[N:13]=1)[C:9]#[N:10].C[CH2:16][O:17]C(C)=O.CCCCCC>CN1CCCC1>[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:17][CH3:16])[N:13]=1)[C:9]#[N:10]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 7359062,6-DichloroisonicotinonitrileHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 58503866HCID 58503866, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 84541-MethylpyrrolidineLösungsmittel

Versuchsvorschrift

In a 25-mL, 3N round-bottomed flask equipped with thermometer pocket fitted with an nitrogen inlet and a rubber septum, NaH (0.112 g, 1.0 eq.), methanol (0.11 mL, 1.0 eq.), suspended in N-methylpyrrolidine (5 mL). The reaction mixture was stir at 25-30 C for 30 minutes. To this reaction mixture 2,6-dichloroisonicotinonitrile was added at 0-5 C. The progress of the reaction was followed by TLC analysis on silica gel with 10% EtOAc-hexane as mobile phase which shows that starting material was consumed after 2 hours staring at 0-5 C. Reaction was quenched by water, precipitate was observed that was filter by filter paper and wash with hexane to give required compound (0.51 g, crude). Reaction was stirred for 20 min with water solid was separated and compound was collected by filtration on a Buchner funnel and washed with of hexane (30 mL); Yield: 0.51 g crude 2-chloro-6-methoxyisonicotinonitrile.

Aufarbeitung

  1. customIn a 25-mL, 3N round-bottomed flask equipped with thermometer pocket
  2. customfitted with an nitrogen inlet
  3. customwas consumed after 2 hours
  4. customReaction
  5. customwas quenched by water, precipitate
  6. filtrationthat was filter
  7. filtrationby filter paper
  8. washwash with hexane

Quellen und Nachweise

ORD-Eintrag
ord-c1d72bb1dd7348c385f766be105920f5
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303000B2

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